7397-68-4

Usage

Uses

Used in Pharmaceutical Industry:
1,3-DIHYDRO-2H-IMIDAZO[4,5-C]PYRIDIN-2-ONE is used as a reactant for the regiospecific preparation of cyclic ureas. This application is significant because the selective protection by alkoxycarbonyl groups allows for the synthesis of specific cyclic urea derivatives, which can be further utilized in the development of pharmaceutical compounds with targeted therapeutic effects.
Used in Chemical Synthesis:
In the field of chemical synthesis, 1,3-DIHYDRO-2H-IMIDAZO[4,5-C]PYRIDIN-2-ONE can be employed as a building block or intermediate for the creation of more complex molecules. Its unique structure and reactivity make it a valuable component in the synthesis of various organic compounds, potentially leading to new materials and applications in different industries.

Upstream product

• 54-96-6 3,4-diaminopyridine 
• 201230-82-2 carbon monoxide 
• 183311-28-6 (3-Amino-pyridin-4-yl)-carbamic acid tert-butyl ester 
• 623562-26-5 3-amino-4-pyridylcarbamic acid methyl ester 
• 904294-61-7 3-amino-4-pyridinylcarbamic acid ethyl ester 
• 57-13-6 urea 
• 1839-17-4 3-amino-4-(methylamino)pyridine 
• 31481-86-4 3-amino-4-hydrazinopyridine 
• 124897-41-2 4-(β-Hydroxyethylamino)-3-aminopyridine 
• 452-58-4 2,3-Diaminopyridine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 623562-22-1 (3-nitro-pyridin-4-yl)-carbamic acid tert-butyl ester 
• 79546-31-9 N-(4-pyridyl) methyl carbamate 
• 98400-69-2 N-(4-pyridyl) t-butyl carbamate 

Downstream Products

• 105953-21-7 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-6-ethoxycarbonyl-1,3-dihyroimidazo<4,5-d><1,2>diazepin-2-one 
• 105953-22-8 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-6-ethoxycarbonyl-1,3-dihyroimidazo<4,5-d><1,2>diazepin-2-one 
• 71703-03-2 4-amino-1,3-dihydro-2H-imidazo<4,5-c>pyridin-2-one 
• 1196074-80-2 1-[(2S)-3-(benzyloxy)-2-hydroxypropyl]-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one 
• 1456504-89-4 (S)-5,5-dimethyl-3-(4-(2-oxo-1H-imidazo[4,5-c]pyridin-3(2H)-yl)phenyl)-4-phenyloxazolidin-2-one 
• 1456504-90-7 (S)-5,5-dimethyl-3-(4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)phenyl)-4-phenyloxazolidin-2-one 
• 105953-07-9 5-amino-1,3-dihydroimidazo<4,5-c>pyridin-2-onium mesitylenesulfonate 
• 105953-14-8 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3-dihydroimidazo<4,5-c>pyridin-2-one 
• 105953-15-9 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3-dihydroimidazo<4,5-c>pyridin-2-one 
• 161468-64-0 3-(Phenylmethyl)-2,3-dihydro-2-oxo-1H-imidazo<4,5-c>pyridine-1-carboxylic acid 1,1-dimethylethyl ester 
• 1025897-33-9 1-(Cyclohexylmethyl)-1,2-dihydro-2-oxo-3H-imidazo<4,5-c>pyridine-3-carboxylic acid 1,1-dimethylethyl ester 

Relevant academic research and scientific papers

1,3-Dihydro-2H-imidazo[4,5-c]pyridin-2-one

A facile acid catalysed cyclisation method for the preparation of the cyclic urea 2H-imidazo[4,5-c]pyridin-2-one (2) in > 95% yield is reported. The biologically active compound 2 can be obtained by heating (3-amino-4-pyridinyl)-carbamic acid methyl, ethyl or tert-butyl esters (1a-c) in sulfuric acid (0.1%) or in aqueous HBF4 (3.5 equivalents) for 10 min. - 3 hrs at 90 °C. The corresponding microwave-promoted (MW) reactions afforded the pure product 2 within few minutes. The 6-butylamino-substituted analogue (2a) was correspondingly obtained by MW irradiation in 99% yield by cyclisation of 2-(butylamino)-5-amino-4-pyridylcarbamic acid isopropyl ester (1d). Quantitative precipitation of product 2 was obtained by pH adjustment. The process represents a solvent-free, "green" method for the preparation of 2.

Rational Design, Pharmacomodulation, and Synthesis of Dual 5-Hydroxytryptamine 7 (5-HT7)/5-Hydroxytryptamine 2A (5-HT2A) Receptor Antagonists and Evaluation by [18F]-PET Imaging in a Primate Brain

We report the synthesis of 46 tertiary amine-bearing N-alkylated benzo[d]imidazol-2(3H)-ones, imidazo[4,5-b]pyridin-2(3H)-ones, imidazo[4,5-c]pyridin-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, oxazolo[4,5-b]pyridin-2(3H)-ones and N,N′-dialkylated benzo[d]imidazol-2(3H)-ones. These compounds were evaluated against 5-HT7R, 5-HT2AR, 5-HT1AR, and 5-HT6R as potent dual 5-HT7/5-HT2A serotonin receptors ligands. A thorough study of the structure-activity relationship of the aromatic rings and their substituents, the alkyl chain length and the tertiary amine was conducted. 1-(4-(4-(4-Fluorobenzoyl)piperidin-1-yl)butyl)-1H-benzo[d]imidazol-2(3H)-one (79) and 1-(6-(4-(4-fluorobenzoyl)piperidin-1-yl)hexyl)-1H-benzo[d]imidazol-2(3H)-one (81) were identified as full antagonist ligands on cyclic adenosine monophosphate (cAMP, KB = 4.9 and 5.9 nM, respectively) and inositol monophosphate (IP1, KB = 0.6 and 16 nM, respectively) signaling pathways of 5-HT7R and 5-HT2AR. Both antagonists crossed the blood-brain barrier as evaluated with [18F] radiolabeled compounds [18F]79 and [18F]81 in a primate's central nervous system using positron emission tomography. Both radioligands showed standard uptake values ranging from 0.8 to 1.1, a good plasmatic stability, and a distribution consistent with 5-HT7R and 5-HT2AR in the CNS.

TRICYCLIC ANILIDE HETEROCYCLIC CGRP RECEPTOR ANTAGONISTS

Compounds of formula I: wherein variables A1, A2, B, m, n, J, R4, G1, G2, G3 and Y are as described herein, which are antagonists of CGRP receptors and which are useful in the treatment or prevention of diseases in which the CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

SPIROLACTAM TRICYCLIC CGRP RECEPTOR ANTAGONISTS

Compounds of formula (I): (wherein variables A1, A2, A3, A4, A5, A6, A7, B1, B2, B3, B4, D1, D2, E1, E2, E3, E4, E5, G1, G2, J, K, T, U, V, W, X, Y and Z are as described herein) which are antagonists of CGRP receptors and which are useful in the treatment or prevention of diseases in which the CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

SPIROHYDANTOIN TRICYCLIC CGRP RECEPTOR ANTAGONISTS

Compounds of formula I: (wherein variables A1, A2, A3, A4, A5, A6, A7, B1, B2, B3, B4, D1, D2, E1, E2, E3, E4, E5, G1, G2, R6, T, U, V, W, X, Y and Z are as described herein) which are antagonists of CGRP receptors and which are useful in the treatment or prevention of diseases in which the CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

TRICYCLIC ANILIDE SPIROLACTAM CGRP RECEPTOR ANTAGONISTS

The present invention is directed to compounds of Formula I: I (where A1, A2, B1, B2, B3, B4, D1, D2, J, K, T, U, V, W, X, Y, Z, R4, R5a, R5b, R5c, m and n are defined herein) useful as antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which the CGRP is involved, such as headache, migraine and cluster headache. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

Preparation of substituted 1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-ones

A new synthetic route to 6-substituted-imidazo[4,5-c]pyridin-2-ons from 4-aminopyridine has been investigated. 4-Aminopyridine protected as alkyl carbamates were nitrated with dinitrogen pentoxide to the corresponding methyl, i-propyl and t-butyl 3-nitropyridin-4-yl carbamates (5a-c) in 51-63% yields. Attempts to substitute these in the 6-position by the ONSH and the VNS techniques succeeded with butylamine and the t-butyl carbamate 9. From the methyl or t-butyl 3-nitropyridin-4-yl carbamates 5a, 5c 1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (1) was formed in 73 and 39% yields, respectively. t-Butyl 6-N-butylamin-3-aminopyridin-4-yl carbamate (6) gave 6-butylamino-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (7) in 53% yield.

Cephem compounds

The present invention relates to novel cephem compounds having the formula: STR1 wherein, Q is a carbon or nitrogen atom; X is an oxygen atom, or a nitroalkyl or cyanoimine group, with the proviso that X cannot be an oxygen atom when Q is a carbon atom; R1 is a hydrogen atom, or a lower alkyl group, or a lower alkyl group which may be substituted by fluoro, or by a carboxylic group or an inorganic cation salt thereof; and R2 and R3 independently are a hydrogen atom or a lower alkyl group; or pharmaceutically acceptable salts thereof. The compounds of the present invention have potent antibacterial activities against gram-negative bacteria, especially Pseudomonas, and a longer half-life than conventional cephem compounds.

3-fused pyridiniummethyl cephalosporins

Novel semi-synthetic cephalosporin derivatives having a fused pyridiniummethyl at 3-position of the cephem nucleus, pharmaceutically acceptable salts, physiologically hydrolizable esters or solvates thereof are disclosed. Also disclosed is a process for preparing the cephalosporin derivatives which comprises introducing a fused pyridiniummethyl substituent at 3-position of 7-β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-carboxylic acid derivatives. The compounds of the present invention show potent antibacterial activities and a broad spectrum against both gram-positive and gram-negative bacteria.

A NEW SYNTHESIS OF HETEROCYCLES VIA CARBONILATION OF AMINES WITH CARBON MONOXIDE IN THE PRESENCE OF SELENIUM

Amines which contain a second functional group in the appropriate position react with carbon monoxide in the presence of selenium to form heterocyclic derivatives in which carbon monoxide is incorporated.For instance, diamines, aminoalcohols, and their related compounds undergo carbonylation to give cyclic ureas, urethanes and the corresponding carbonylated compounds.For diamines and amino alcohols with more than two carbon atoms between the functional groups, intermolecular carbonylative coupling takes place competing with the intramolecular reaction.High selectivity has been attained under specified reaction conditions.Anilines having cyano or acetyl groups on the ortho position afford new classes of selenium-containing heterocycles.In these reactions, carbamoselenoate has been suggested as the common key intermediate.